He first made his mark on Hearts' first team during a pre-season tour of Austria in 2006, where he started all three friendlies, creating four goals in the process with his direct play and crossing ability. In August 2006 Driver signed a five-year extension to his contract with Hearts, committing him to the club until 2011. He made his home debut in the league on 26 August 2006 against Inverness Caledonian Thistle, coming on as a substitute with 15 minutes to go and scoring four minutes later.[3] Driver also scored a free kick in a 3–1 victory over Celtic at Celtic Park on 29 April 2007.[4] In July 2008 Driver signed an amended contract with the club for another five years committing himself to the club until 2013.[5]

Driver was the subject of two bids totalling £500,000 from Championship club Burnley in the summer of 2008, which was rejected by Hearts.[6]Coventry City too made a £1 million bid in the 2009 January transfer window, which was also rejected. On 6 July, the BBC reported that Burnley had opened signing talks with Hearts.[7] Joop Munsterman the FC Twente CEO reported on RVT Oost that Hearts had turned down a £3m offer for Driver.[8] In all five clubs enquired about his availability including Chelsea.[9]

Since the Summer of 2010 Driver's appearances were limited due to injury.[10] A bad knee injury needed surgery[11] and was followed by a thigh injury suffered during a bounce match to regain fitness.[12] In May 2011 he had to undergo a further knee operation.[13]

In his first appearance on his return from Injury Driver made his European debut against Paks in the Europa League scoring the third goal in their 4-1 win.[14] Despite being fit[15] Driver only appeared in seven of the first 20 competitive appearances under new manager Paulo Sérgio and a loan deal was considered,[16] but did not come to fruition as Hearts were seeking a fee for the loan.[17]

Driver's finest moment in a Hearts jersey came on 19 May 2012, as the Tynecastle club faced their rivals Hibernian in the final of the Scottish Cup, defeating them 5-1, with Driver putting in an excellent performance.

On 16 December the press reported that Driver was due to hand in a transfer request[18] as he no longer wished to play under new manager Paulo Sérgio.[19] The following day he was included in the squad as a substitute to face Dunfermline but was dropped after confirming to Sergio that he did not wish to play under him.[20] Despite this Driver was a 62nd minute substitute against Motherwell the following weekend replacing David Templeton.[21]

Driver made his league debut on 17 March 2013 against FC Dallas, where he also scored in the 79th minute.[24]

He won MLS "Man of the Match" honors after scoring the match-winner vs. L.A. Galaxy on 5 May 2013 in a regular season rematch of the prior two MLS Cup finals [25] He then scored against D.C. United on 8 May 2013.

On 25 November 2014, it was announced that Houston had declined the option on Driver's contract.[28] On December 8, 2014, his rights were traded to D.C. United, who opted not to sign him after a short trial.[29]

He was thought to be eligible to play for the Scotland senior team because of the new residency ruling recently introduced.[32][33] He was not called up by then-manager George Burley as Burley stated that it was Driver's choice to officially make himself available for selection.[34] On 4 February 2010, Driver committed his international future to Scotland after face-to-face talks with Scotland manager Craig Levein.[35] Only one week after opting to represent Scotland, the Scottish FA informed Driver he was not eligible to play for the national team, as he had not been schooled in Scotland for the requisite period of time.[36] This rule was subsequently altered to allow Driver to play for Scotland,[37] although he is yet to do so.